Being rich in America is just so draining. You have to unwind someplace:

[cali]

And oh the irony. Sinclair Lewis wrote about the corruption of the monied classes extensively. He must be spinning in his grave.

And after all, a cottage for $2,500 or so a night includes meals and activities.

http://www.twinfarms.com/accommodations

[HughBeaumont]

1. If you're wealthy, you HAVE a house like that and HAVE a view like that.

Bizarre shit going on in the CEO Larceny Cult. It's as if most things they do in the corporate world and otherwise is being done for the sake of; 'nother words, "because they CAN".

[cali]

2. Not always and very few of the wealthy have a 5 to 1 ratio staff

that caters to your every whim, a 4 star chef, high level at home spa services, personal at home fly fishing coaches and tennis coaches and no most of the wealthy don't have art collections anywhere near that caliber.

[Ikonoklast]

3. You are absolutely correct.

Some of them have even more than that.

[Atman]

4. Oh, I would totally go there!

Next time I hit the lottery. We spend a lot of time in Vermont, but I've never seen anything like this. I checked for reservations, and a ROOM starts at about $1500. But you need to check out the "amenities." This is an all-inclusive, like Sandals, only much nicer and in the Vermont mountains. Everything is included, all your meals, liquor, wine, recreation, and all rooms/suites/cottages feature fireplaces, twice daily maid service, same-day laundry service and a LOT more. They even say they'll unpack and pack for you. Is it crazy expensive? Yes...the OP's suggestion of $2,500 a night for a cottage was low. The cheapest cottage I could find was over $3000 a night. Maybe next year.

[cali]

5. If I could ever afford something like that again (and didn't feel too guilty)

I'd return to the Travaasa Hana again on Maui- much cheaper, great amenities and great service and it's on the ocean- or Caneel Bay on St. John in the U.S. VI or Long Bay on Tortola or this place on Virgin Gorda which I love and is all inclusive including sailing: https://www.beyc.com/index.php/stay/premium-beachfront-cottages

[Atman]

6. If you can deal with the airfare...Thailand.

Best place ever. Not the mainland, head out the islands. Samui has a large ex-pat community, so English isn't really a problem. And it is wicked cheap. I mean, like...we traveled over there with just one backpack each. Partied on the beach with my sister and friends, then when the sun set, we walked up the beach to a five-star resort. We got a private villa with it's own swimming pool (with an outdoor king-sized canopy bed next to it), an outdoor bathroom with carved granite tub, fantastic restaurant with dining on the beach...for less than what it cost us to spend the night at a Motel 6 at JFK the night before we flew out. Beers are about 50 cents, and you can get one in the airport and walk around anywhere with an open beer. Ferry trips to the other islands were phenomenal, diving trips cost less than a new pair of fins and a mask. Unbelievable place. But it takes about 20 hours of air time to get there.

[kpete]

7. donuts for the rich

It looks like a gilded lotus flower crossed with a spaceship - but it’s actually a Krispy Kreme doughnut worth £1,000.

http://www.buzzfeed.com/robynwilder/presenting-the-worlds-most-expensive-doughnut